Sulfuric Acid → 2,6-Dichloro-4-methylnicotinamide

HRID 1899388Notes

Reaction equation

HRID 1899388 reaction equation
[C:1]([C:3]1[C:4]([Cl:11])=[N:5][C:6]([Cl:10])=[CH:7][C:8]=1[CH3:9])#[N:2].S(=O)(=O)(O)[OH:13]>>[Cl:11][C:4]1[C:3]([C:1]([NH2:2])=[O:13])=[C:8]([CH3:9])[CH:7]=[C:6]([Cl:10])[N:5]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 701313-Cyano-2,6-dichloro-4-methylpyridine

Product 1

HCID 3348552,6-Dichloro-4-methylnicotinamide

Procedure

3-Cyano-2,6-dichloro-4-methylpyridine (80g, 0.42 mole) was dissolved in concentrated sulfuric acid (440ml). The mixture was heated at 150° C.-170° C. with stirring for 30 minutes, cooled and poured on ice. The precipitate was filtered and washed with water. The wet filter cake was dissolved in methylene chloride, washed, neutralized with Na2Co3, dried over Na2SO4 (anhydrous), and concentrated until a white precipitate separated. Petroleum ether was added, the crystals were filtered and dried at room temperature overnight to give 83g (94%) of 2,6-dichloro-4-methyl-3-pyridinecarboxamide.

Workup

  1. temperatureThe mixture was heated at 150° C.-170° C.
  2. temperaturecooled
  3. additionpoured on ice
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. dissolutionThe wet filter cake was dissolved in methylene chloride
  7. washwashed
  8. dry with materialdried over Na2SO4 (anhydrous)
  9. concentrationconcentrated until a white precipitate
  10. customseparated
  11. additionPetroleum ether was added
  12. filtrationthe crystals were filtered
  13. customdried at room temperature overnight

Sources & evidence

ORD record
ord-f1819e4061cd400591b4d681702704c6
Source dataset
uspto-grants-1996_11
Patent number
US05571912

Reaction notes

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